Thionyl Chloride → 3-(Tribromomethanesulfonyl)benzoyl chloride

HRID 1934299Notes

Reaction equation

HRID 1934299 reaction equation
[Br:1][C:2]([Br:16])([Br:15])[S:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9](O)=[O:10])(=[O:5])=[O:4].S(Cl)([Cl:19])=O>CN(C)C=O>[Br:1][C:2]([Br:16])([Br:15])[S:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([Cl:19])=[O:10])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 224660403-(Tribromomethanesulfonyl)benzoic acid

Product 1

HCID 224660413-(Tribromomethanesulfonyl)benzoyl chlorideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 375 g (0.86 mole) of 3-tribromomethanesulfonyl benzoic acid were added 1 ml of dimethylformamide and 500 ml of thionyl chloride and the mixture was refluxed for one hour. The reaction mixture was filtered and 3000 ml of hexane was added to the filtrate to precipitate crystals. The crystals were recovered by filtration and dried to obtain 366 g of 3-tribromomethanesulfonyl benzoylchloride (yield 94%, white crystals).

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. filtrationThe reaction mixture was filtered
  3. addition3000 ml of hexane was added to the filtrate
  4. customto precipitate crystals
  5. filtrationThe crystals were recovered by filtration
  6. customdried

Sources & evidence

ORD record
ord-52cce440902b464aaab2bb83479dbb9c
Source dataset
uspto-grants-2002_05
Patent number
US06383731B2

Reaction notes

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